Houses Longboat Key

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Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Rental types Iron Staffed property Golf course on site or within 15 min walk

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Price per night from

$149

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White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Iron

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Price per night from

$630

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Iron, Staffed property

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Price per night from

$436

+++ Clean & Bright +++ Minutes to Anna Maria Island

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Iron, Staffed property

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Price per night from

$178

Cozy & Bright+++Minutes to Anna Maria Island, IMG Academy and more

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Iron, Staffed property

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Price per night from

$117

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“It was very cozy and comfortable apartment!” We loved to spend our vacation at this place. Really close to the beach, to different restaurants, and all kind of stores.

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Iron, Staffed property

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Price per night from

$115

March 23-March 30, 2024 Springbreak 3bdr on the beach Longboat key

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Iron, Staffed property

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Price per night from

$745

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Iron, Staffed property

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Price per night from

$284

Stunning & Serene +++ Minutes from Anna Maria Island, IMG Academy and more!

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Iron, Staffed property

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Price per night from

$114

Responds fast! avg. 0 minutes

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Iron

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Price per night from

$229

Mid Century Home With Private Heated Pool

Tallevast house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Iron

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Price per night from

$182

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Iron

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Price per night from

$287

Responds fast! avg. 11 minutes

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Iron, Staffed property

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Price per night from

$132

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Iron

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Price per night from

$108

Beautiful Longboat Key Home!

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 27 minutes

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Iron

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Price per night from

$516

Rare Castle Style Stay! Downtown

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Iron

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Price per night from

$212

A Pearl of a Beach Home - now with luxury Saltwater heated pool and hot tub

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Perfect Luxury” Our 5-week stay at this vacation rental was absolutely perfect. The house was everything you could ask for and more. We have stayed in many vacation rentals in the last 20 or so years that we have been coming to anna Maria Island and I have to say this one was right at the top of the list. The kitchen was outfitted with everything you could want. The beds were very comfortable. The neighborhood was nice and quiet. Short walk to the beach. The owners were very nice to deal with and always responded quickly and were very warm and helpful. Definitely can recommend this vacation rental.

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Iron

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Price per night from

$476

Anna Maria Island/ IMG Academy/ Beach/ HotTub/ Bikes/ Kayaks/ Golf/ Fishing

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Iron

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Price per night from

$287

Gorgeous Pool Home. 12 min from the beaches of Anna Maria, IMG

Bradenton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Iron

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Price per night from

$281

#7 Loft Apartment in Historic District Downtown Sarasota

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Iron

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Price per night from

$305

Siesta Key Beach : 2 Bedroom, 3 Beds, 3 Bathroom Duplex & Heated Pool

Siesta Key apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Iron

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Price per night from

$182

Stunning & Bright Sarasota Home

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Iron, Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$395

Modern Lakerfront Condo! 2x Pools~WiFi~Lanai. By IMG~Beaches~Restaurants~AMI~SRQ

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 11 minutes

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Iron

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Price per night from

$138

Florida Palms Heaven 2B Villa, near tennis IMG Academy & beaches

South Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Iron

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Price per night from

$148

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Iron

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Price per night from

$205

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Iron

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Price per night from

$148

Rambo's Beach Retreat! Tradewinds Unit 14

Bradenton Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Iron

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Price per night from

$453

Anna Maria Island Beach Watch

Bradenton Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Iron, Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$251

Anna Maria Island Beach Happy-Direct Beach Front-1BR-1BR

Bradenton Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Iron, Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$231

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Golf course on site or within 15 min walk, Rental types, Iron, Staffed property

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Price per night from

$344

Luxury Resort Sleeps 26!

Palma Sola house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 26

Responds fast! avg. 3 hours 39 minutes

3 of 4 match: Golf course on site or within 15 min walk, Rental types, Iron, Staffed property

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Price per night from

$2,289

ZILLI VILLA

Longboat Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Iron

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Price per night from

$487

2 of 4 match: Iron, Staffed property, Rental types, Golf course on site or within 15 min walk

2 of 4 filters match

Price per night from

$229

Anna Maria Island Beach Palace

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Iron, Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$605

Anna Maria Island Beach Haven

Cortez house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Iron, Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$1,500

AMI Gulf Lookout-Views Of The Gulf From Every Room-Rooftop Terrace

Cortez house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Iron, Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$385

Anna Maria Island Surfside Bungalow

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Iron, Staffed property, Rental types, Golf course on site or within 15 min walk

2 of 4 filters match

Price per night from

$355

Anna Maria Island Edgewater Bungalow

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Iron, Staffed property, Rental types, Golf course on site or within 15 min walk

2 of 4 filters match

Price per night from

$298

Viewing 38 of 909
rentals in Longboat Key

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